The LeanScale Podcast · Episode 87

Most Acquisitions Fail Like This: What Nobody Tells You About M&A

Chris Heller (CRO, Place) on M&A integration, talent as the ultimate leverage, and the career moves that actually compound

Chris Heller · Chief Revenue Officer · Place Hosted by Anthony Enrico
Published Updated 00:43:21 37 min read 7,373 words
Mergers & Acquisitions Sales Leadership GTM Strategy Revenue Operations
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Executive Summary

The one-paragraph brief, extended

Why this conversation matters — and who should spend the hour.

Chris Heller is not a typical CRO. He got his real estate license as a sophomore in college, sold timeshares at Lake Tahoe to make summer money, and then — knowing nothing about the job on day one — sold 27 homes his rookie year when the average agent sold six or seven. He never slowed down: 100-plus homes a year for 26 consecutive years, one of the top 10 agents out of 37,000 nationally, then number one in North America. From there he became CEO of Keller Williams Realty, where he doubled the size of the company and more than doubled its profitability between 2010 and 2017, before going on to run mellohome (the homeownership arm tied to a top US mortgage lender), serve as President of OJO Labs, and now sit as the first-ever Chief Revenue Officer at Place. This conversation with LeanScale co-founder Anthony Enrico mines a 35-year career for the handful of principles that actually compound.

The spine of the first half is leverage. In 1989 — when it was unheard of for a solo agent — Chris hired an assistant so he could stop stuffing envelopes and spend his hours helping people buy and sell homes; that one 'logical conclusion' became the operating model that scaled him to a full team. His modern version of the same lesson: talent is the number-one form of leverage and always will be, with technology (now machine learning and AI) a close and compounding second. He and Anthony go deep on the magnitude most leaders underestimate — the hidden tax of a B-player who quietly drags the whole system down, versus the A-player who, like Michael Jordan's 'no days off' standard, unconsciously raises everyone's game. The practical takeaways: always be recruiting even when you have no open role, hire for track record and resilience, and deliberately hire people who are better and smarter than you so they push the organization instead of you having to pull them.

The middle of the episode reframes career strategy. The most reliable way to earn the next opportunity, Chris argues, is to be extraordinary at what you're doing right now — every opportunity in his career came to him unsolicited because of the results he was producing. He also makes an unusually candid case for creating space: after leaving Keller Williams he forced himself to do nothing for six months, read 'The Surrender Experiment,' and learned that when you stop trying to force an outcome, the right path tends to reveal itself. When it is time to choose, he uses a values-vs-opportunities chart — non-negotiables like trust, integrity, and a believable path to winning down one axis, opportunities across the other — and refuses to deviate from his standards for a deal that merely looks good on paper.

The back third is a two-sided clinic on mergers and acquisitions. If you're the one being acquired, control what you can control: your reaction and your openness, and — if it's your company — whether the cultures genuinely fit. If you're the acquirer, the single biggest predictor of a successful integration is how and when you bring people along, and relentless over-communication. Chris's sharpest tactic is the first all-hands: skip the company history and financials and answer the only question employees actually have — am I safe, and what does this mean for me? Anthony adds his own lived example from Emailage's acquisition by LexisNexis, a textbook integration that left employees with a clear plan. Handled badly, the cost is brutal and measurable: you lose good people who shouldn't have left, and with them congruency, momentum, and value.

Who should listen: founders and CEOs weighing an acquisition or a career move, revenue executives and CROs inheriting a team through integration, and any sales or GTM leader trying to understand why talent density beats almost everything else. The biggest takeaway of the hour is that the same principle — leverage through people, applied with clear values and honest communication — is what compounds across a top producer's book, a global company's P&L, and the messy human middle of an M&A deal.

Key Takeaways

14 things worth stealing

The load-bearing ideas, each with the business implication and who should care.

01

Talent is the #1 form of leverage — technology is #2

Chris has believed forever that the most important thing is just talent: you have to have really talented people, and there's no replacement for that. Technology — now machine learning and AI at a level unimaginable a few years ago — is a powerful and compounding second, but it multiplies talented people rather than substituting for them.

Why it matters: Invest first in talent density, then arm those people with the best available tools. Leaders who chase tooling to paper over a mediocre team get neither leverage nor results.

FoundersSales LeadersRevenue ExecutivesRevOps Leaders
02

The B-player tax is bigger than anyone realizes

Even when a B-player can do their job okay, they don't help the people around them level up, they require constant help, and they quietly drain the whole system. The cost of not building a team of A-players, Chris says, is greater than most people ever understand — the reverse of the A-player who immediately raises everyone's standard.

Why it matters: Treat every hire as a signal to the rest of the team. One tolerated B- or C-player tells your A-players you're not building a championship team, and the best ones will notice.

Sales LeadersRevenue ExecutivesFounders
03

A-players set a 'no days off' standard the whole team absorbs

The best analogy is sports: when Kobe joined the Lakers he instantly leveled up everyone around him, and Michael Jordan's teammates said the biggest thing they learned was 'no days off' — practices harder than the games. An A-player unconsciously pulls the standard of excellence up across the team.

Why it matters: You don't have to mandate a culture of excellence if you hire for it — a few genuine A-players will raise the bar for effort and standards more effectively than any policy.

Sales LeadersRevenue ExecutivesFounders
04

Always be recruiting — even when you have no open role

Chris is always looking, even when he doesn't need anyone. Conferences are 'always productive' because he's constantly scouting people to hire, companies to buy or partner with. When the need finally comes up, he already knows exactly who to call.

Why it matters: Build and maintain a live bench of talent before you need it. Recruiting under pressure, from a standing start, is how teams settle for the B-player they can find today.

Sales LeadersRevenue ExecutivesFounders
05

Hire for track record and resilience — and for people better than you

There's no substitute for a track record of results; that's the evidence someone knows what to do. Then look at resilience — when they got knocked down, did they play victim and blame the market, or take responsibility and come back better? And for any role, hire people better or smarter than you at it, so they push the organization instead of you having to pull them along.

Why it matters: Screen for demonstrated results plus how a candidate responded to failure, and resist the ego pull to hire people you can out-perform. The people who push you are the ones who scale the company.

Sales LeadersFoundersRevOps Leaders
06

The most reliable career strategy is to be extraordinary at what you're doing now

Every opportunity in Chris's career came to him unsolicited — he never asked for the executive role, the CEO seat, or the CRO job. They came because he produced extraordinary results. His advice to anyone angling for the next thing: whatever your role, even a restaurant server, just be the best in the building and opportunities will find you.

Why it matters: Stop hunting for shortcuts to the next title. Extraordinary output in your current seat is the most durable and least competitive path to the next one.

FoundersSales LeadersRevenue Executives
07

Create space before the next move — the six-month sabbatical

After leaving Keller Williams, Chris forced himself to do nothing for six months and read 'The Surrender Experiment.' The lesson: when you stop trying to force an outcome and relax into things, the right path shows up and you gain clarity. When one door closes, a whole bunch of doors open — you just have to give it enough time to see them.

Why it matters: You don't need the next thing lined up before you leave the current one. Deliberately creating space — in a job or a relationship — is what lets you actually see and take the right opportunity.

FoundersRevenue Executives
08

Use a values-vs-opportunities chart for every big decision

Chris runs every major change through a simple chart: down the vertical axis, the things that matter most to him (people, trust, integrity, emotional safety, belief in the vision, a path to winning, mutual respect); across the horizontal axis, the different opportunities. Then he checks which boxes each one hits — so a role that's exciting or lucrative but checks only three of 17 boxes reveals itself.

Why it matters: Make your non-negotiables explicit before you evaluate options. A structured values screen turns a seductive 'this pays more' into a clear-eyed comparison of what will actually make you effective and fulfilled.

FoundersRevenue ExecutivesSales Leaders
09

Never deviate from your non-negotiables for a good-looking deal

Trust, respect, and integrity are non-negotiable, and it's never worth deviating from your standards for a situation because it never works out — the things you know matter will surface later. Shared vision and a believable path to winning have to be there too; no amount of money is worth a situation that costs you sleep or self-respect.

Why it matters: When a deal or role is missing your fundamentals, the size of the opportunity won't rescue it. Walk before you rationalize the gap away.

FoundersRevenue Executives
10

Culture and values alignment is the real predictor of M&A synergies

Post-close champagne assumes synergies will just materialize, but if the companies aren't culturally aligned it becomes immensely difficult to realize them. Cultural fit, Chris argues, shows up in real financial results — and when you're the one in control of a deal, making sure the cultures match is one of the most important things you can do.

Why it matters: Diligence the culture as hard as the numbers. Misalignment that looks cosmetic pre-close becomes the reason the modeled synergies never show up in the P&L.

FoundersRevenue Executives
11

When you're acquired, control the only thing you can — your reaction

If your company is being acquired and it's not your call, the deal itself is out of your control. What is in your control is how you approach it: whether you judge and resist it, or embrace it and go in with an open mind to create opportunities. That posture shapes both your experience and the success of the transition as much as anything.

Why it matters: Coach acquired teams to focus energy on their response rather than relitigating the deal. The employees who approach integration as a blank slate come out of it with the opportunities.

Revenue ExecutivesFoundersSales Leaders
12

Over-communication is the single biggest predictor of a successful integration

Nothing is more important than communicating, over-communicating, and inviting questions. When Chris isn't getting a lot of questions from an acquired team, he worries — they should have many, and he wants the space where they're comfortable asking so he can answer, be authentic, and build the relationship. When that doesn't happen, both sides discover harmful things only after close.

Why it matters: Build deliberate, high-frequency communication channels through the transition and treat a lack of questions as a red flag, not a green light. Silence is where integrations quietly fail.

FoundersRevenue ExecutivesRevOps Leaders
13

In the first all-hands, answer 'am I safe?' before company history

Chris once stopped a people-ops leader who was deep into the acquirer's history, financials, and vision, and told the acquired employees the truth: right now all you care about is how this impacts you and whether your job is safe. Reading the audience and addressing what they actually care about lets people go home and say 'this sounds exciting' instead of 'maybe we should cancel our vacation.'

Why it matters: Sequence integration communication around the employee's real fears first. Leading with corporate narrative when people are worried about their jobs squanders the most important meeting of the deal.

FoundersRevenue Executives
14

Bad integrations lose the good people who shouldn't have left

What a bad integration looks like is people leaving — before, during, and after — including people who would have had great opportunities but didn't feel safe, didn't see a plan, or weren't communicated with. Some attrition is natural, but when good people leave who shouldn't have, you lose talent, congruency, momentum, and value. Anthony's Emailage/LexisNexis integration is the counter-example: a clear plan and leadership introduction that made people feel there was a path.

Why it matters: Judge integration success by retention of the people you most wanted to keep. Psychological safety and a visible plan are what stop your best people from pulling the ripcord.

Revenue ExecutivesFoundersRevOps Leaders
Frameworks Discussed

8 named models

Every framework Jimmy names, defined and time-stamped.

Talent First, Technology Second

11:55

A two-tier model of leverage: the number-one and permanent form is talent — genuinely great people — and the number-two, fast-compounding form is technology (today, machine learning and AI). Technology multiplies talented people; it does not replace them.

Chris frames leverage as the through-line of his whole career, from hiring the first assistant in 1989 to arming modern go-to-market teams with AI. The ordering matters: tools amplify a strong team and paper over nothing on a weak one, so talent density is the prerequisite for technology leverage to pay off.

The A-Player Standard (No Days Off)

13:48

The principle that a true A-player raises the standard of everyone around them, while a B- or C-player imposes a hidden tax that drags the whole system down. Illustrated by Kobe leveling up the Lakers and Michael Jordan's teammates learning 'no days off.'

The magnitude is what leaders underestimate: the cost of tolerating a B-player is greater than most ever realize, because excellence and mediocrity are both contagious. Building a team of A-players is less about any single hire's output than about the standard the whole team absorbs.

Always Be Recruiting

16:05

The discipline of continuously scouting talent even with no open role — treating every conference, meeting, and relationship as sourcing — so that when a need arises you already have a list of people to call.

Because there's no substitute for hiring proven talent, and proven talent is rarely available exactly when you need it, Chris keeps a live bench at all times. It converts hiring from a reactive scramble into drawing from a pre-qualified pool.

Track Record + Resilience + Hire People Better Than You

17:07

A three-part talent screen: a demonstrated track record of results (evidence they know what to do), resilience (how they responded to getting knocked down — ownership vs. victimhood), and hiring people who are better or smarter than you at the role.

Track record is the evidence, resilience is the character test, and the 'better than you' filter is the leverage test: people better than you push the organization forward, while people you out-perform have to be pulled along. Together they define what a talented hire looks like.

Be Extraordinary at What You're Doing Now

21:00

The career thesis that the surest way to earn the next opportunity is to be extraordinary in your current role, so that results — not networking or shortcuts — pull opportunities to you unsolicited.

Every role Chris landed came to him because of the results he was already producing. The counterintuitive advice for ambitious young people angling for the next title: stop hunting shortcuts and simply become the best in whatever seat you're in — opportunities follow evidence of excellence.

Creating Space (The Surrender Experiment)

22:15

The practice of deliberately creating a gap — Chris forced himself to do nothing for six months — before the next move, on the premise that when you stop forcing an outcome, the right path and clarity show up.

Named for the book that mirrored his experience, the idea is that fear, anger, or the urge to line up the next thing act as a filter that blocks you from seeing opportunities. When one door closes, many open; space is what lets you see and take the right one.

The Values-vs-Opportunities Chart

30:25

A decision matrix with a person's non-negotiable values down the vertical axis (people, trust, integrity, emotional safety, belief in the vision, a path to winning, mutual respect) and the candidate opportunities across the horizontal axis, scored by which boxes each opportunity checks.

Chris runs every major change through this chart so that an exciting or lucrative option that only satisfies a few of his core values is exposed for what it is. Getting crystal-clear on what you don't want — often learned the hard way — is what makes the screen work.

Over-Communication & the 'What Does This Mean for Me?' All-Hands

39:57

An M&A integration playbook whose single biggest success factor is how and when you bring people along and relentless over-communication — including a first all-hands that answers employees' real question (am I safe, what does this mean for me) before any company history or financials.

Bring people along at the appropriate time for their protection, invite questions and treat their absence as a warning sign, and read the audience so the acquirer addresses fear first. Done well it builds trust and retention; done badly, good people leave and you lose congruency, momentum, and value.

Best Quotes

18 lines worth clipping

Pulled verbatim. Copy or share any of them.

“I wake up and eat what I kill every day and I'm really good at hunting and killing, but I wanna build something.”
Chris Heller 02:51
“It was a logical conclusion to come to that I needed to create leverage.”
Chris Heller 09:23
“I think the most important thing is just talent. You have to have really talented people. There's no replacement for that. So that's number one. Number two is technology.”
Chris Heller 11:55
“The tax that you pay when you bring a B player onto the team — even if they can do their job okay, they're not helping everyone else around them level up.”
Anthony Enrico 13:04
“The cost of not doing that is greater than most people ever understand or realize.”
Chris Heller 13:48
“It was no days off. Once Michael was there, our practices were harder than the game. That's what an A player does — they level up and cause the rest of the team to up their game.”
Chris Heller 14:27
“Even when I don't need someone, I'm looking. If you're always looking for talent, you may not need them, but when the need comes up, you know who you're gonna call.”
Chris Heller 15:50
“I want people that are better or smarter than I am at it. If they aren't, then I'm likely having to pull them along. If they are, they're gonna be pushing me and that's what I want.”
Chris Heller 17:45
“Just be the best damn server in that restaurant and opportunities will come. That's where opportunities come from — being extraordinary in whatever you're doing right now.”
Chris Heller 18:33
“When you're not trying to force an outcome or create an opportunity, and you just relax into things, the right things show up. The right path shows up. You gain clarity.”
Chris Heller 21:13
“When one door closes, another one opens. The truth is, when one door closes, a whole bunch of doors open. You just have to give it enough time to see them and find them.”
Chris Heller 24:03
“It's never worth deviating from your standards for a situation, 'cause it never works out.”
Chris Heller 31:44
“On your last day, none of that stuff's gonna matter. What's gonna matter is, do you look back and say, hey, I had a good adventure and I think I made an impact and I think I made a difference.”
Chris Heller 34:02
“There's nothing more important than communicating and over communicating and asking questions.”
Chris Heller 36:05
“Right now, all you care about is how this is going to impact you — are you safe, is your job safe. These are human beings, and we have to make sure that we're caring for them.”
Chris Heller 38:54
“When I was at Emailage, we went through that acquisition process. LexisNexis did a great job of that. I remember leaving those meetings feeling like, okay, there's a plan, the team knows what they're doing.”
Anthony Enrico 40:05
“When good people leave when they shouldn't have, that's when it wasn't handled well. You lose talent, you lose congruency, you lose momentum, you lose everything.”
Chris Heller 41:22
“I know everything I do is preparing me for the next thing.”
Chris Heller 43:14
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Founders

  • Build talent density first and layer technology on top of it — talent is the number-one form of leverage, and AI multiplies great people rather than rescuing mediocre ones.
  • Before you sign an acquisition, diligence culture and values as hard as the numbers; misalignment is why modeled synergies never show up in the P&L.
  • When you create space between roles, give yourself real time — Chris forced six months of doing nothing — and trust that clarity and the right opportunity show up when you stop forcing an outcome.
  • Make your non-negotiables explicit and refuse to deviate from them for a lucrative-looking deal; it never works out.

Revenue Executives

  • Treat over-communication as the single biggest lever in any integration — invite questions relentlessly, and worry when a team you're acquiring isn't asking any.
  • Sequence the first post-deal all-hands around employees' real fear — 'am I safe, what does this mean for me' — before company history, vision, or financials.
  • Judge integration success by whether you kept the people you most wanted to keep; losing good people who shouldn't have left is what a botched integration actually looks like.
  • When you inherit a team, read the room and create psychological safety fast, or people will withhold information and quietly start looking for the exit.

Sales Leaders

  • Always be recruiting, even with no open role — keep a live bench so you never have to settle for the B-player available today.
  • Screen candidates on track record and resilience, and deliberately hire people better and smarter than you so they push the team forward.
  • Protect the standard: one tolerated B- or C-player tells your A-players you're not building a championship team, and the best ones notice.
  • Coach your team that the surest path to the next role is being extraordinary in the current one — results pull opportunities to you unsolicited.

RevOps Leaders

  • Frame your own value as leverage: find the highest-impact activities and offload or automate the rest, the modern version of Chris hiring an assistant in 1989.
  • Plan the operating model and communication cadence of an integration before close so the revenue engine keeps its congruency and momentum through the transition.
  • Protect institutional knowledge during change — people who don't feel safe withhold information, and that's where value quietly leaks.
Operations Takeaways

By function

The same conversation, filtered for RevOps, pipeline/marketing ops, and customer ops.

Revenue Operations

  • Leverage is the operator's job. The 1989 assistant hire is the timeless RevOps move — find the highest-impact activities, offload or automate the rest, and reinvest the freed capacity in revenue-generating work.
  • Talent density beats tooling. Technology (including AI) multiplies great operators; it doesn't rescue a weak team. Build the bench first, then arm it.
  • Protect the revenue engine through integration. Plan the operating model and communication cadence before close so an acquisition keeps its congruency and momentum instead of leaking value.
  • Psychological safety protects institutional knowledge. People who don't feel safe withhold information; a clear plan and relentless communication are what keep the team — and its knowledge — intact.

Customer Operations

  • Retention is decided in the first meeting. In an acquisition, address employees' real question — am I safe, what does this mean for me — before anything else, or you lose the good people you most wanted to keep.
  • Silence is a red flag. A team that isn't asking questions during a transition isn't calm — it's disengaged or fearful. Invite questions relentlessly and treat their absence as a warning.
  • Bad transitions bleed talent. Handled badly, integration means good people leave who shouldn't have — and you lose congruency, momentum, and value with them.
  • A visible plan builds trust. Anthony's LexisNexis example — a leadership introduction and a clear integration plan — is what let employees leave the room feeling there was a path forward.
Metrics Mentioned

The numbers, with context

27 homes
Rookie-year home sales

Chris's first year as an agent, knowing nothing on day one, versus the average agent's six or seven — good for Rookie of the Year in San Diego.

100+ homes/year for 26 years
Sustained production

Chris sold over 100 homes a year for 26 consecutive years — far more than the '4x the average' framing, closer to 20x the typical agent.

Top 10 of 37,000
National ranking

Chris became one of the top 10 agents out of the 37,000 in his first national company.

#1 of ~80,000
Scale ranking

At his more entrepreneurial company he became the number-one agent in North America out of roughly 80,000 agents before taking an executive role.

2x size, 2x+ profit (2010–2017)
Keller Williams growth

As CEO, Chris doubled the size of Keller Williams and more than doubled its profitability from 2010 to 2017, expanding into 20-plus countries.

1989 assistant
First leverage hire

Chris hired an assistant as a solo agent in 1989 — unheard of at the time — to offload low-value tasks and focus on revenue-generating work.

6 months
Sabbatical length

Chris forced himself to do nothing for six months after leaving Keller Williams, an uncomfortable but formative exercise in creating space.

June 2020
Pandemic acquisition close

OJO Labs closed a large, opportunistic acquisition of the fifth-largest (only privately owned) real-estate search portal in June 2020, when almost no one else was buying.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

PlacePropTech

Chris Heller's current company, where he is the first-ever Chief Revenue Officer, brought in by the founder (a friend of 15 years) to own the revenue side after the two co-founders divided focus elsewhere.

00:00 · 07:12Company →
Keller Williams RealtyReal Estate

Where Chris rose from top-producing agent to CEO of Keller Williams Realty International; between 2010 and 2017 he doubled the size of the company and more than doubled its profitability while expanding into 20-plus countries.

04:21Company →
OJO LabsPropTech

The 2019 startup Chris joined as President after sitting on its board; six months in it made a large, opportunistic acquisition that closed in June 2020, at the height of the pandemic.

05:49 · 06:30Company →
mellohomeReal Estate / Mortgage

The homeownership arm tied to a top US mortgage lender, where Chris served as CEO after leaving Keller Williams and his six-month sabbatical.

05:06Company →
LowerMortgage / Fintech

The national mortgage company that acquired OJO Labs; Chris references selling 'that company last year' to a national mortgage company before moving on to Place.

06:30Company →
EmailageRisk & Fraud

Anthony's company, acquired in early 2020 (announced February, closed amid the pandemic); its integration into LexisNexis is Anthony's lived reference case for a well-run acquisition.

19:56 · 40:05Company →
LexisNexis Risk SolutionsData & Risk Analytics

The Fortune 1000 acquirer of Emailage; Anthony credits its integration as excellent — flying out, renting an auditorium, introducing the leadership team, and presenting a clear plan that made the transition successful.

20:33 · 40:05Company →
ZillowReal Estate Marketplace

Named as the reference point for the online real-estate search portal OJO Labs acquired in 2020 ('similar to Zillow or realtor.com').

06:30Company →
Realtor.comReal Estate Marketplace

Named alongside Zillow as the comparison for the fifth-largest, only privately owned real-estate search portal OJO Labs bought in 2020.

06:30Company →
Carrabba's Italian GrillRestaurant (anecdote)

Where Anthony worked for six years starting at 16 (busing, hosting, then running the whole bar at 19) — his personal illustration of Chris's 'be extraordinary now, opportunities follow' principle.

19:13Company →

People

Chris Hellerguest

First-ever CRO of Place; former top-producing agent and CEO of Keller Williams, with 35+ years across real estate and mortgage technology.

Chief Revenue OfficerProfile →
Anthony Enricohost

Co-founder of LeanScale and host of The LeanScale Podcast.

Co-FounderProfile →

Tools & software

Methodologies referenced The Surrender Experiment
Related LeanScale Services

Where this shows up in the work

Fractional RevOps

Embedded, field-facing RevOps leadership and execution — the operator model Jimmy describes, delivered as a service.

Chris's whole career is a study in leverage and building the revenue engine — the embedded, revenue-owning operator model LeanScale delivers as a service.

Sales Enablement Build

Stand up a zero-based, sales-academy enablement motion sized to your span of control and sales complexity.

The talent-density thesis — A-players, the B-player tax, hiring people better than you, and raising the whole team's standard — maps directly to how LeanScale stands up and levels up sales teams.

AI for GTM

Agents and workflows that multiply operator throughput — the 'make humans superhuman' thesis, operationalized.

Chris's 'talent first, technology second' framing is the premise behind LeanScale's AI-for-GTM work: tools that multiply strong operators rather than replace them.

Frequently Asked Questions

Straight answers

Generated from the conversation, marked up for search and AI extraction.

Why do most acquisitions fail?

According to Chris Heller, acquisitions fail on the human integration, not the deal math. The biggest predictor of success is how and when you bring people along and how relentlessly you over-communicate. When culture and values aren't aligned and employees don't feel safe or informed, good people leave who shouldn't have — and you lose talent, congruency, and momentum. Handled well, integration keeps the team intact and the synergies real.

What is the single most important factor in a successful M&A integration?

Communication — specifically over-communication and inviting questions. Chris worries when an acquired team isn't asking a lot of questions, because they should have many; he wants a space where people feel comfortable asking so he can answer authentically and build trust. When that communication doesn't happen, both sides discover harmful surprises only after the deal closes.

What should you say in the first all-hands after an acquisition?

Answer the only question employees actually have first: am I safe, and what does this mean for me? Chris once stopped a colleague who was deep into company history, financials, and vision and redirected to the employees' real concern. There's plenty of time later to learn about the acquirer; in the first meeting, reading the audience and addressing their security is what lets people go home feeling the change is exciting rather than threatening.

Is talent or technology the bigger source of leverage?

Talent — and Chris believes it always will be. His model is talent first, technology second: you have to have genuinely talented people because there's no replacement for that, and technology (now machine learning and AI) is a powerful, fast-compounding multiplier on top of them. Tools amplify a strong team but can't rescue a weak one, so talent density is the prerequisite for technology leverage to pay off.

What is the hidden cost of hiring a B-player?

It's larger than most leaders realize. Even if a B-player can do their job adequately, they don't help the people around them level up, they require ongoing help, and they quietly drain the whole system. Worse, tolerating a B- or C-player sends your A-players the message that you're not building a championship team. An A-player does the opposite — like Michael Jordan's 'no days off' standard, they unconsciously raise everyone's game.

How do you evaluate talent when recruiting?

Chris looks for three things: a track record of results (the evidence someone knows what to do), resilience (whether they took responsibility and came back better after being knocked down, or played victim), and — for any role — people who are better or smarter than he is at it. People better than you push the organization forward; people you out-perform have to be pulled along. He also recruits constantly, even with no open role, so he always has someone to call.

How does Chris Heller decide whether to take a new job or make a career move?

He uses a values-vs-opportunities chart: down one axis are his non-negotiables (people, trust, integrity, emotional safety, belief in the vision, a path to winning, mutual respect), and across the other are the opportunities, scored by which boxes each one checks. It exposes when an exciting or lucrative option only satisfies a few of his core values — and he refuses to deviate from his standards for a deal that merely looks good on paper.

Why does Chris recommend creating space before your next move?

After leaving Keller Williams he forced himself to do nothing for six months and read 'The Surrender Experiment.' The lesson: when you stop trying to force an outcome and relax into things, the right path and clarity show up. Fear, anger, or the urge to line up the next thing act as a filter that blocks you from seeing opportunities — and when one door closes, a whole bunch of doors open if you give it enough time to see them.

Timeline

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00:00Intro: from real estate license to CEO of Keller Williams 01:22The career origin story: timeshares, 27 homes in year one, rookie of the year 08:13What made Chris 4x more productive than the average agent 11:55Modern-day leverage: talent first, technology second 13:48The hidden cost of B-players and the Michael Jordan standard 16:05How to recruit when you don't need anyone (yet) 21:00Why the most reliable career strategy is being extraordinary at what you're doing now 22:15The six-month sabbatical and "The Surrender Experiment" 27:13M&A part one: what to do when your company is being acquired 30:25The values-vs-opportunities chart Chris uses for every career decision 37:18M&A part two: what makes a target company stand out to a buyer 39:57Why over-communication during integration is the single biggest success factor 42:05The all-hands mistake: knowing what employees actually want to hear first
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00:00Intro: from real estate license to CEO of Keller Williams

0:00 - Today I have Chris Heller, Chief Revenue Officer of Place. Chris is not your typical CRO. He has a incredibly interesting career, gaining his real estate license as a sophomore in college, and then working his way to being the top rep in the world for the company that he worked with. And he's had a stellar career in sales and technology. Today, Chris is gonna go deep on what it takes to get to the Chief Revenue Officer position, what it means to lead a go-to-market organization at scale, and one of the topics that so many companies have troubles with, mergers and acquisitions. How to make that a success, and not just a headache for the organization.

0:48 Chris, thank you so much for being here today. Really, really excited to dive into some of these topics, especially on the M&A side, because I think that's something that's really unique to where a lot of people just don't have experience in that area. But I would love if you could walk us back to the beginning of your career and how you got to what you're doing today. - Yeah, I would say there's probably no connection other than having done it between the beginning and where I am now. I was a sophomore in college. My dad called me and said, "Hey, you're gonna get your real estate license "and come up to Lake Tahoe and sell timeshares

01:22The career origin story: timeshares, 27 homes in year one, rookie of the year

1:22 "for the summer to make some money." And I said, "Okay." And I did that, and that summer job turned into a... Actually, he then took a position in San Diego. We moved to San Diego for the rest of the summer. And then that summer job continued on for three years. Growing to school part-time, working every day because they would let me, and I was making a lot of money. And then I got burned out. Like I just couldn't do it anymore. It's a grind, it's a hard sale. And it was, as a young person, good way to learn skills and make money, but certainly not a career. I had met a real estate broker like three years earlier who kept recruiting me, sending me no cards,

2:06 calling me every time I saw him, wanting me to come work for his broker. And he caught me at a weak moment one day and I said, "Okay, I'll give it a try." I had bought a townhome right before my 21st birthday. And so I knew what owning real estate was, but I had no idea what a real estate agent did. Literally my first day, I was like, I knew nothing. But just through sheer determination and grit and willing to do whatever it took, that first year I sold 27 homes. The average agent will sell six, seven homes a year. I was Rookie of the Year in San Diego. And then every year after that, increased the number of homes I sold

2:51 till I was one of the top 10 agents out of the 37,000 in the national company that we were part of. Stayed there for 16 years, building a great business, making great income and building a family and all that stuff. And then woke up one day and said, "I could keep doing this for a while." But the minute I stop, it stops. Like there's, I wake up and eat what I kill every day and I'm really good at hunting and killing, but it's, I wanna build something. And there were no opportunities within the company. I, through a twist of events, ended up at another company that was much more entrepreneurial where you could own businesses and have a sales team.

3:42 And I did that and those businesses became successful. After three or four years, I was actually the number one. At that point, we had probably 80,000 agents. I was number one in the country. The company was only in North America. It was number one in North America. And then the next year, I took an executive role with the company. The CEO called and said, "Hey, we have something we wanna do and we think you'd be the person to do it. Are you interested?" And I was like, "Yeah, now I had no idea on how to do what they wanna get done or how I was gonna do it." I had like no clue whatsoever, but it sounded like a big opportunity.

4:21 It was a big opportunity and I liked challenges. So I took that. My job was to expand the company globally. So over the next five years, we expanded into over 20 different countries that became very successful. And when there was a leadership change, I was the obvious person to take over running the company. So I became the CEO. That company was Keller Williams Realty. And in the 2010 to 2017, we doubled the size of the company and more than doubled the profitability of the company. And I grew globally as well as domestically. And then decided to make a change and left not knowing what I was gonna do. In fact, forced myself for the first time in my life

5:06 not to do anything for six months, which was an interesting exercise to go through. I mean, Anthony, I'm sure you can relate to this and most listeners can. It was for every day of my life, I had a mission every day when I woke up. And then to not have that was like a real adjustment, but a good one and a good thing to force myself to do. But after about six months, just through happenstance, which has always happened in my career, there was introductions made. And next thing you know, I'm being offered to become the CEO of the sister company of the second largest lender in the country. And did that all the while.

5:49 I was also involved with a lot of startups as an investor, as an advisor on the board. One of the companies I was on the board of in 2019 was really taking off. The mortgage industry was in a slump. So we weren't really able to do much where I was and felt like a racehorse in the starting gate and the gate wouldn't open. And so I joined the startup, became the president of the company. Six months later, we made a very large and opportunistic acquisition that was only be able to, this was in, it closed in June of 2020, right? Little thing called the pandemic started hit in May, I mean in March of 2020. So we were probably the only company crazy enough

6:30 to go get a bunch of money and do a big acquisition. We bought a search portal similar to Zillow or realtor.com. We bought the fifth largest one, the only privately owned one. And so, and the only reason we were able to buy it 'cause no one else was thinking about buying anything right in March, April and May and June of 2020. We sold that company last year and to a national mortgage company. And then decided I didn't want to stay on with that company. Just didn't want to keep doing the same thing I've been doing for the previous five or six years. And a friend of mine who's the founder of Place, who'd been after me for several years

7:12 to come and help him and join the company. And their biggest need was in someone that was really focused on the revenue side of the business. The two co-founders had sort of divided and conquered and were focused on other parts of the business and no one was waking up every day saying, okay, how can we optimize our revenue opportunities and make sure that we're monetizing the things we should be monetizing? And that's how I ended up where I am right now. - That's a fantastic story. And one of the things I'm really curious about, I'm sure has been a through line throughout your entire career. If you don't mind going back to when you were an agent

7:52 doing 4X the volume and productivity of the average agent, is there something there that you were doing that is applicable across sales roles in general? What was making you so successful? - Yeah, actually for the last 26 years, I sold over 100 homes a year for 26 consecutive years. So I was doing much more than 4X the average. I like to think I was just using common sense and logic. And I was, but then I was also developing my skills at a very high level. And so when I say common sense and logic, Anthony, what I mean is at the end of my first year, just through, sure, blood, sweat and tears, figuring out how to do things,

08:13What made Chris 4x more productive than the average agent

8:42 I literally worked every day and I worked ungodly hours. I was probably at the office at 6.30 in the morning and sometimes I'd come home for dinner and then go back to work or not come home for dinner. And at the end of that year, I was like, I can't, how am I gonna sell any more homes than I did this year? I can't work any harder, I can't work any longer. I don't wanna work harder or longer. I wanna actually have a life too. So the only logical conclusion I came to is I had to hire someone to do some of the stuff I was doing so I could focus on the high impact or the revenue generated activities. So I hired an assistant.

9:23 Now back, this was in 1989, a long time ago, for a real estate agent to have an assistant was unheard of. I was in an office with 60 or 70 people and the agents, most of which were all older than me, were like, what are you doing? Who do you think you are, the president or something? Hiring an assistant and I'd look at them and say, well, you've been stuffing envelopes for the last two and a half hours. I'm gonna pay someone to do that so I can be helping more people buy and sell homes. So it was just like, it was a logical conclusion to come to that I needed to create leverage. And so that continued on. So as I became more successful

10:03 and then started to develop my skills at a higher level and become a real professional salesperson, I needed more help. And so that assistant grew to two assistants and then to agents and people to help show properties and do different activities so that I could keep selling more. Almost like a doctor's office, going from the old time doctor who made house calls to now a modern day doctor that has a receptionist and an insurance person and a PA and a lab tech and all those people so they can see lots of patients. That's how I developed my business. So it was just taking a business approach to things. I actually, from the very beginning, had a bookkeeper

10:50 and had a P&L that I looked at every month when most agents didn't even know what a P&L meant. So it was just a business approach and a very process approach. And then there was a very disciplined approach. I became extremely disciplined in certain areas that allowed me to be a lot more efficient and a lot more effective. - Yeah, definitely personally as a founder, learning how to focus myself on higher leverage things and upgrading along the growth of lean scale has been something continually trying to do. From a go-to-market perspective, what does modern day leverage look like? 1989, it meant, hey, hiring a system

11:31 when nobody else was even thinking about doing that. When you're leading go-to-market teams now, what are the best ways they're getting the most leverage possible? - Well, I still, and this has been true forever and I think will probably be true forever, I think the most important thing is just talent. You have to have really talented people. There's no replacement for that. So that's number one. Number two is technology, especially now. I mean, we're all leveraging machine learning and AI at a level that wasn't even imaginable a few years ago. And that creates a lot of leverage.

11:55Modern-day leverage: talent first, technology second

12:20 I started my first company in 2020 as an agent but a side business of developing some software for real estate agents. And so I've always been involved or I've been involved with technology for a long time. I don't consider myself a technologist. I'm not an engineer, I'm not a product person, but I've understand the power of it and the benefits and how to leverage. And that is whether it's go-to-market, whether it's any other part of the business, we have to make sure that we're leveraging the tools that are available to the high extent if we wanna maximize our leverage. - Yeah, going to the talent comment you made,

13:04 I think it took me a little bit of time to recognize this. I think everybody knows there's a big difference between an A player and a B player. I don't know if people really understand the magnitude of difference and the tax that you pay when you bring a B player onto the team because even if they can do their job okay, they're not helping everyone else around them level up. They're usually requiring a little bit of help here and there, so it just drains the overall system. But when you put an A player into the field, you just immediately recognize they're leveling up everyone around them. They're doing 2X, in your case in real estate,

13:40 you're doing 20X the output, doing 100 houses to the average of five or six. It's dramatically different if you can get your team full of A players. - Yeah, it's, and you're right, like the cost of not doing that is greater than most people ever understand or realize. You know, the best analogy is sports. Like if you look at, you know, the championship teams, I don't know, pick a sport basketball. You know, when Kobe came to the Lakers, immediately leveled up everyone else. Like his standards for excellence, his standards, you know, Michael Jordan. I saw an interview recently of one of Michael Jordan's former teammates and said, you know, what was the thing

13:48The hidden cost of B-players and the Michael Jordan standard

14:27 that you learned most or the biggest impact? And he said, it was no days off. Once Michael was there, it was like, you know, we practice harder, our practice were harder than the game. So they were like, that's the thing that we learned. And so that's what an A player does. The true point, they level up and it causes the rest of the team to up their game. At the same time, if we bring in people that are B or C players, we're unconsciously sending a message and it's the wrong message if you're trying to build, you know, a championship team, whether it's in business or in sports. So, you know, it's something that I think people intuitively know is important,

15:10 but I don't think they really understand how important it is. - I'm always curious how, we definitely have our methods for who we're looking for, who we're recruiting, how we suss them out before making a decision. In your experience, you've built so many sales teams, go-to-market teams, are there things you're looking for? Are there ways you can test this in the recruiting process? Because I feel like that's the most difficult part. - It's definitely things I'm looking for and I'm always looking, right? So even when I don't need someone, I'm looking. Yeah, there's a lot of, we have a lot of industry conferences and I'll get the question all the time.

15:50 Oh, how was the conference? Or was it productive? And I said, there always is. 'Cause I'm always looking for either someone to hire or someone that I wanna hire at some point, looking for an opportunity for either a company to buy or partner with, right? So if you're always looking for people and looking for talent, you may not need them, but when the need comes up, you know who you're gonna call or you have a list of people you're going to call. So that's one thing, just always be looking. And then there's no substitute for a track record, right? There's no substitute for someone who has a track record of success or of getting results.

16:05How to recruit when you don't need anyone (yet)

16:31 You know, when I look back at like in my own career, every opportunity I've gotten, I didn't ask for any of them. I didn't like try to seek them out or create them or anything else. They all came from me getting extraordinary results and then people come into me and say, "Hey, we do this." You know, and I'm not looking to make a move or anything else, but if I were, the last thing I'd be worried about was what I was gonna be doing next 'cause I know there'd be more opportunities than I would ever want or could choose. The biggest challenge is always choosing the right one. So you look for people that have gotten great results

17:07 because that's the evidence that they know what to do. And then there's other characteristics too, right? You look for people that are resilient because people that have gotten knocked down and how do they respond when they get knocked down? Were they a victim about it? Do they blame situations, the market, circumstances, or do they take responsibility and get up and become better because of what they went through? Those are all characteristics of talented people. So you look for those characteristics. You look for what their track record. Another one that I always look for is I just, for whatever the role is,

17:45 I want people that are better or smarter than I am at it.

17:50 If they aren't, then I'm likely having to pull them along. If they are, they're gonna be pushing me and that's what I want. I want people pushing the organization, pushing me, pushing the company. And that's what talented people do. - 100% right. And I think it's tough to be patient. And to your point, you find great talent because you've been focused on it. You've been investing in it. In some cases, I'm sure years, sounds like you went to work with a former friend that they know your character, they know your track record. So these things are built up over years. It's not impressing someone in an interview process. So yeah, you have to always be vigilant.

18:33 And I think the best way to get the next best thing is to do the work that's on your plate extraordinarily well right now. - Yeah, yeah, especially for young people, everyone wants opportunities. Everyone wants something more than what they have. And they're always angling on how to do it or how to get there quicker or what's the shortcut. The most surefire way, I don't care what role you're in. You could be a server in a restaurant. Just be the best damn server in that restaurant and opportunities will come. You're gonna get offers to manage. You're gonna get offers from customers that see like, oh my gosh, this person's phenomenal

19:13 in their customer service or they're phenomenal in their communication or whatever. It's like, that's where opportunities come from is being extraordinary in whatever you're doing right now. - It's funny that hits home really well for me. I worked six years at Carabas Italian Grill, very proud of that experience, School of Hard Knocks. And I started at 16, busing, hosting. And then at 19, it would go like server, then bartender. And at 19, I was running the whole bar, doing the ordering, everything, like I can't even drink, but I'm running the bar. And yeah, that came from busing the table as well. - Yeah, 100%.

19:56 - One thing I wanna go back to that you brought up and you asked if I've had this experience and I certainly have when you take a break. One of those times that happened, I was at a company called Emailage. It got acquired in 2020. It was in March, crazy time 'cause it was February when we made the announcement, not everything started getting shut down yet. And so like the LOI was there, but it hadn't really closed yet. And that's when the NBA shut down, airports started shutting down and we were wondering like, hey, is this deal gonna close or not? God willing, it did close. But what ended up happening after that,

20:33 I was working at Lexus Nexus and big Fortune 1000 company. And I really didn't have anything to do. And it was the pandemic. So I was just kind of sitting at home. And I think that was one of the most challenging years of my life being in a position where there wasn't a lot of work to do. I was maybe working a handful of hours a day and I was just going crazy and I needed the next thing. Is there anything that you felt like you learned in the boredom about yourself or about what to do next during that time? - Yeah, it's a really good question. I read a book at that time, which I have recommended to numerous people

21:00Why the most reliable career strategy is being extraordinary at what you're doing now

21:13 who are going through transitions or those things. And the book was called "The Surrender Experiment". It's a great book and it's actually a true story of the author. And what he talked about in that book is what I experienced firsthand. And that is that when you're not trying to force an outcome or create an opportunity or anything else, and you just relax into things, and this is gonna sound a little woo woo, but the universe, the right things show up, right? The right path shows up. You gain clarity. And so there was an adjustment period where I was like for the first time in my life, not waking up knowing exactly what I needed to do

22:02 and what I wanted to accomplish and everything else. And that created a little anxiety at the beginning, like getting used to that and like not knowing how to react to that and missing that, like I gotta go do this thing or accomplish that thing or, you know. But then as I forced, and I literally forced myself. Like I said, hey, I'm not gonna make any decisions for six months. I'm not gonna do anything. About three and a half months into it, I did meet the founder of a company, highly successful, his third company, self-made billionaire, and I ended up going to work for him about three months later, maybe about four months later, it took a while.

22:15The six-month sabbatical and "The Surrender Experiment"

22:46 But I didn't seek that out. That just happened. Like I got a phone call one day of someone who wanted to talk about my role at Keller Williams and I informed him. He didn't know I wasn't there anymore. He said, oh, well, you know, if you're ever in the area, we'd still love to talk to you. And a few months later, three months later, I was in the area that began that journey. But, you know, I just learned that, yeah, I learned a lot. Learned about patience, learned about letting go, learned about, you know, being able to be quiet enough to see and hear, you know, the right messages. And I've advised a lot of people, like, you know,

23:26 a lot of people go, oh, I gotta figure out what I'm gonna be doing. I gotta have something before I get rid of this thing. It's like, I know it feels that way, but you don't. In fact, there's, and whether it's relationships, whether it's a job, like creating that space to not do anything, I think is so important, so valuable. - Yeah, and sometimes you need that space to even take advantage of an opportunity because if you had been, you know, still deep in with whatever your current mission was, it maybe holds out an opportunity for that to pop up. Or like you said, would you have had that conversation? Would you have had the open time to go do that?

24:03 Sometimes you need that to make some magic happen. - I think not sometimes, I think always, I really do. I mean, there's, you know, there's that old adage, you know, when one door closes, another one opens. The truth is, when one door closes, a whole bunch of doors open. You just have to give it enough time to, you know, to see them and find them. There's never a shortage of opportunities. There's just our, you know, sometimes it's our inability to see them, you know, because we're either scared or fearful or angry or whatever, and you can't see opportunities when you're experiencing any of those reactions. So whenever there's a change that happens,

24:47 whether it's a change of career or an external change, something in our country or in the world or in our company, you know, if we resist that or get angry about that or get fearful about it or don't like it or any of those things, it creates a filter that prevents you from seeing opportunities. You can't be in that space and see opportunities at the same time. - Right, right. And I think for those who are listening that might be in a role, they feel like maybe it's not in their zone of genius or in a situation where maybe it's not going where they want to go. Sometimes letting go first will be the thing that opens up those doors. - For sure.

25:29 - One area I'd really like to spend some time with you on, 'cause I think I can learn a ton, our audience can learn a ton, is your experience with mergers and acquisitions. It looks like you've been on both sides of the deal. You've gone through deep levels of integrations. How, a lot of people will maybe go through that process maybe once or twice. What has been your experience with that and what advice would you give maybe on either side of the deal? If you're getting acquired, if you're looking to buy a company, and what does it take to make it really valuable on the other end of it? - Yeah, so those are two very different experiences, right?

26:15 If you're being acquired or acquiring. So let's talk about if you're being acquired. And it depends on your role too, right? If it's your company or if you're just someone in the company that's being acquired. Many times you don't have control, right? Like if you work at a company, that company is being acquired, that's out of your control. Now what is in your control is how you react to it, how you approach it. Are you judging it? Are you resisting it? Are you embracing it? Are you trying to create a blank slate and go into it with an open mind to see and create opportunities? So like that impacts your experience

26:56 and the success of that transition as much as anything. If you're the one in control, if it's your company, then I think you, one of the most important things is just making sure culturally that it's a fit and it's a match, right? And being really clear on what's important to you. I think that's another thing that is a big miss for a lot of people. If you've ever, and most of us have, been in a relationship and that relationship ended, you get really clear on what you don't want in the next relationship. Like when I got divorced, I didn't know if I wanted another relationship, but I knew what I didn't want. Like I was crystal clear on what I didn't want.

27:13M&A part one: what to do when your company is being acquired

27:43 And so whether you go through something that causes you to get that clarity, or you force yourself to like make a list. I have a chart I've used every time that I've made a change, right? I decided to leave the company after we got acquired, or I decided to join this company or leave that company. I just created a chart and I have on the vertical access, all the things that are important to me, right? Like the people, trust, integrity, safety, emotional safety, do I believe in the vision and the company?

28:24 Do I see a path to winning? Are these people I respect and who respect me? Like those are all the things that are really important to me. And then across the horizontal access are just the different opportunities and just check off. All right, does this opportunity check that box? Does it check this box? Does it check that box? So you can really see, hey, this one sounds more exciting or it could be more lucrative, but it only checks three of my 17 boxes or whatever the case may be. So it helps give you clarity when you know what's important to you and what you like and what you don't like. I was talking to someone just this earlier this week

29:10 who's making a career change and CEO of a company, looking at some other opportunities. And this person was talking about the nuts and bolts of her options and the financial parts. And I said, hey, which one are you gonna have the most fun in? Which is gonna be with people you'd like and respect? And because here's what I know. If you're not in a good environment, the amount of energy that you have to expend to manage that is intense. And it takes a toll, takes a toll on the quality of your life and everything else. When you're in an environment, I was in a role leading a company, but because of some of the board members and everything else,

29:56 it had to spend more energy managing relationships and the situations and the dynamics than I did on doing the job. And that was exhausting and was not fulfilling in any way, shape or form. So if I'm gonna spend energy doing something, I want doing positive things. So I know it's a long-rounding answer to your simple question, but I think those are some of the things that are super important. - Well, I think a lot of people don't highlight the culture alignment aspect enough. And I think that comes out in real financial results too. So post acquisition, great. Champagne's popped, hopefully, unless it's like a fire sale type situation.

30:25The values-vs-opportunities chart Chris uses for every career decision

30:43 But people are excited about it. We're anticipating synergies and we're gonna realize this. But if you're not culturally aligned, I think it can be immensely difficult to pull that off. Are there any, like knowing your values, knowing who you are, are there any other big red flags like, hey, I know maybe on paper this looks good, but I don't know if we're really gonna realize the synergies and value if we make this happen. - Yeah, I think, so from like a leadership perspective, like I said, and these are personal for me, but these are like non-negotiables, like trust and respect and integrity, like those, and those are all kind of interrelated,

31:27 but those have to be there. Like it can't be, well, yeah, they might be a little bit of this, but the situation's so good or the opportunity's so good. It's never worth deviating from your standards

31:44 for a situation, 'cause it never works out. Like those things are gonna come up, those things that you know that are important to you that aren't there. Shared vision, like are you aligned with the vision? Is there, and do you see a path to winning? Like when I took this role, I spent a lot of time. In fact, even though I've known this person for 15 years, he was, we were in a conversation with someone else, and he said, yeah, Heller put me through the ringer for several months, 'cause I had lots of conversation, lots of really trying to suss out how he thinks and how he, to make sure that we were aligned on things,

32:27 versus just jumping in and then finding out that there's this big disconnect or something else. The other thing is, and this becomes, it becomes more apparent as you get older, but the, again, the old cliche, life is too short. Like to be in situations that aren't optimal or that aren't fueling you or fulfilling you, it's not worth it. There's literally, to be in a bad, there's no amount of money that could cause me to be in a bad situation that I just didn't like or that caused me not to be able to sleep at night or feel good about myself or what I was doing. It's just not worth it. - Yeah, totally agree. And even if you did pay,

33:20 like what are you gonna use the money for if you're having a miserable day every single day? So I think the hypothesis is I make more money and I'll be able to afford a better life, but if that's not even on the table in the situation, then what's the point? - Yeah, and there's no guarantee that you'll have that life, right? Things happen all the time to people. So there's no, you could say we're all on borrowed time. So, and at the end of the day, on your last day, none of that stuff's gonna matter, right? What's gonna matter is, do you look back and say, hey, I had a good adventure and I think I made an impact and I think I made a difference

34:02 and those are the only things that are gonna matter. - I love that, absolutely. Did you have a good adventure? I think, did you impact the people and did you live a life you're proud of? Hanging on to the M&A topic a little bit, you've been on the buying side. So you probably have an unfair advantage potentially have, you're looking at multiple companies when a lot of companies are getting acquired, maybe that's happening to them for the first time. What would you say tends to help a company stand out, make that process successful? Sounds like cultural alignment's a huge one in doing that, but are there any things that are like,

34:44 man, this killed a deal or hey, this got us really excited about me rallying my company to make this deal happen? - Okay, so you're talking about, has the company been acquired, what stands out? What should you be doing to make it a problem? - Yeah, since you have that perspective of being the buyer, you're out looking for them, what stands out? Good, Erwin. - Yeah, so here's what I've seen work and here's what I've seen not work. How you bring your people along and when you bring them along is critical. I've seen people do it at a really high level where they've, 'cause anything can happen in any transaction, right? None of them are guaranteed to close.

35:27 So if you don't wanna make an announcement to the whole company early on, oh, this is what we're doing. Now, the company may know that you're looking at opportunities and merger opportunities and acquisitions and a lot of them are gonna need to know that 'cause they're gonna be asked to provide data and diligence information. But bringing them along at the appropriate times for their protection is really important. The companies that don't do that tend to have a lot of swirl and then you have a bunch of people that don't understand why the deal's happening to begin with, that have opinions about it or have judgment about it or you know,

36:05 and then you have this internal battle that's going on while the founder's trying to keep a smiley face with the acquirer, he's dealing with a bunch of chaos or she's dealing with a bunch of chaos that they really created themselves. - The other thing is just communication. I mean, there's nothing more important than communicating and over communicating and asking questions. Like if I'm not getting a lot of questions, you know, from the people of the company that we're acquiring or from the leaders, I'm like, I'm worried about that 'cause they should have a lot of questions and I want them to ask them and I want to be able

36:45 to have them create that space where they're comfortable asking them and that they can, which gives me an opportunity to give them answers and for them to see that, you know, I'm being real and authentic and truthful with them, right? That's an important foundational piece to building that relationship. The other, and when that doesn't happen, you know, then the deal closes in, you know, now you're discovering things or finding out things or they're discovering things or finding out things or, you know, that are counterproductive or actually harmful to what you're trying to accomplish or whether it's integrating the companies

37:18M&A part two: what makes a target company stand out to a buyer

37:24 or, you know, building the business or, you know, taking it from, you know, where it is to there. Those are all things that get in the way of that. So like communication is always a huge one. How the founder or leaders of that company are handling it with their team to bring them along. Then, you know, also the acquiring company, you know, how they address the team and make them feel is a critical component to it. You know, when we meet with the new team for the first time, you know, whether it's pre-closing or post-closing, you know, really understanding where they're at. I'll give you an example. This was actually not very long ago.

38:10 We had a meeting with this team and we had a person from our team, sort of a people ops leader, who was leading this like this interaction. And this person was going really heavily into, you know, our company and the history and the financials and where we're going and this and that. And I had at one point just stop and say, stop that person and say to the employees of the company, say, hey, you're going to have plenty of time to learn about us. I know right now, all you care about is how this is going to impact you and what does this mean to you and are you safe and is your job safe and everything else, right? So it was, you know, knowing the audience

38:54 and reading the audience and being able to address the things that they care about and that are important to them so that, you know, they can, you know, go home that night and tell their partner or their spouse or, you know, hey, this is what's happening and this sounds really exciting versus, I don't know what this means and we shouldn't, you know, maybe we should cancel our vacation because I don't know if I'm going to have a job, right? Like these are human beings and we have to make sure that we're, you know, caring for them in a way that helps them do their job and be productive and not, you know, create challenges for them.

39:33 - Yeah, and if you're not creating that environment of psychological safety, then it's going to be very difficult as you navigate the integration process. You'll have people looking, thinking, hey, maybe I'm going to get fired. I should start looking and leave. They may withhold information so that way they have certain value and a lot of people will perceive that. So I think that's an unbelievably important thing to do. And when we, when I was an email agent, we went through that acquisition process. LexisNexis did a great job of that. They flew out, we rented like a giant auditorium. The whole company could go in.

39:57Why over-communication during integration is the single biggest success factor

40:05 They introduced their whole leadership team and had a plan for how integration was going to work and what was next. And I remember leaving those meetings feeling like, okay, there's a plan, team knows what they're doing. And I think that made the integration really, really successful. - 100%, yeah. When you've been through it, you know what works and what doesn't work. - Yeah, I was fortunate to go through a good one, but I could see where if they didn't do that, I don't know if you have any horror stories of, hey, we didn't do this upfront or we delayed XYZ during the integration process and it caused trouble. I don't know what it looks like when it's bad.

40:43 - Absolutely. I mean, what it looks like when it's bad is a lot of people leave, right? A lot of people leave before, during and after. And people that shouldn't have, right? And people that would have had great opportunities, but they didn't, you know, things weren't handled the right way. And so they didn't feel safe or they didn't see or things weren't communicated with them. So they, you know, they pulled the grip cord, excuse me, and, you know, and jumped. So, you know, that's, those are the ones that aren't, those are the ones that aren't handled well. 'Cause in a, you know, look, there's always gonna be some people that leave

41:22 'cause maybe it's the right thing for them to leave or the best thing or they have an opportunity, but those happen anyways. But it's when good people leave when they shouldn't have, that's when, you know, it wasn't handled well. And that's what it looks like when it's not handled well is you lose talent, you lose congruency, you lose momentum, you lose, you know, everything. - Chris, that's really insightful on making those integrations and acquisitions successful. And I can kind of see the through line just across your career and how you've approached either your job managing a team, managing a company, looking for acquisitions that make sense.

42:03 I love that it's always tied to core values and doing the right thing at the right time. And I really appreciate everything you shared. I think anyone listening has an opportunity to learn quite a bit, whether you're in that sales role, just knowing, hey, it's gonna take level of effort focusing on high leverage things. I think that's gonna always apply, especially today with opportunities to leverage AI and other tools to give yourself more leverage. And then I think everything you shared with, especially going through a career transition, if you don't give yourself the opportunity to give yourself that space, sometimes you may be missing out

42:05The all-hands mistake: knowing what employees actually want to hear first

42:37 on opportunities that are waiting for you. So have the courage to do that when appropriate. And some of the biggest moments in people's professional lives, that merger acquisition that happens, staying true to your values and making sure you're creating a environment of psychological safety, and then making sure there's a path to winning together, I think highly important. Even if it looks nuts and bolts on paper look good, we have to make sure those things are aligned. So I've learned a ton. Chris, just thank you so much for everything. And I can't wait to see what you do next. - Thank you. I'm always looking forward to what's next.

43:14 And I know everything I do is preparing me for the next thing. So appreciate the opportunity to share and hope this was valuable.